Zirconium-promoted ring opening. Scope and limitations

Organometallics

Volumn 15, Issue 4, 1996, Pages 1208-1217

  Cénac, Nathalie ^a   Zablocka, Maria ^b   Igau, Alain ^a   Commenges, Gérard ^a   Majoral, Jean Pierre ^a   Skowronska, Aleksandra ^b  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^b CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3042750574     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950491+     Document Type: Article

References (45)

1. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
2. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
3. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
4. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
5. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
6. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
7. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
8. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
9. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
10. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
11. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
12. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
13. Tetrahedron Symposia in print No. 57; Negishi, E., Guest Ed. Tetrahedron 1995, 51, 4255. For reviews see for example: (a) Annby, U.; Karlsson, S. Acta Chem. Scand. 1993, 47, 425. (b) Labinger, J. A. Comprehensive Organic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 3, Chapter 3, p 667. (c) Negishi, E. Ibid, Paquette, L. A., Ed.; Vol. 9, Chapter 5, p 1163. (d) Ryabov, A. D. Chem. Rev. 1990, 403. (e) Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1991, 403, 133. (f) Erker, G.; Aulbach, M.; Mena, M.; Pfaff, R.; Sosna, F. Chem. Scr. 1989, 29, 451. (g) Negishi, E. Ibid. 1989, 29, 457. (h) Negishi, E.; Takahashi, T. Synthesis 1988, 1. (i) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (j) Negishi, E. Acc. Chem. Res. 1987, 20, 65. (k) Erker, G. Acc. Chem. Res. 1984, 17, 103. (l) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 6, 333.
14. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
15. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
16. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
17. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
18. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
19. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
20. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
21. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
22. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
23. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
24. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
25. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
26. See for example: (a) Wailes, P. C.; Weingold, H. J. Organomet. Chem. 1970, 24, 405. (b) Lipshutz, B. H.; Kato, K. Tetrahedron Lett. 1991, 32, 5647. (c) Tucker, C. E.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 9888. (d) Venanzi, L. M.; Lehman, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (e) Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1992, 33, 7461. (f) Karlson, S.; Hallberg, A.; Gronowitz, S. J. Organomet. Chem. 1992, 430, 53. (g) Treilhou, M.; Fauve, A.; Pougny, J.-R.; Prome, J.-C.; Veschambre, H. J. Org. Chem. 1992, 57, 3203. (h) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (i) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (j) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 34, 341. (k) Schedler, D. J. A.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1993, 34, 5035. (l) Chemin, D.; Linstrumelle, G. Synthesis 1993, 4, 377. (m) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett. 1993, 33, 341.
27. Wipf, P.; Smitrovich, J. H. J. Org. Chem. 1991, 56, 6494.
28. Cénac, N.; Zablocka, M.; Igau, A.; Majorai, J. P.; Pietrusiewicz, M. Organometallics 1994, 13, 5166.
29. Wipf, P.; Xu, W. Synlett. 1992, 33, 718.
30. (a) Hanzawa, Y.; Ho, H.; Ito, Taguchi, T. Synlett 1995, 4, 299.
31. (b) Ito, H.;Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y. J. Am. Chem. Soc. 1994, 116, 5469-70.
32. (c) Annby, U.; Karlsson, S.; Gronowitz, S.; Hallberg, A.; Alvhäll, Svenson, R. Acta Chem. Scand. 1993, 47, 425-33.
33. (d) Cuny, G. D.; Buchwald, S. L. Organometallics 1991, 10, 363.
34. (e) Buchwald, S. L.; Nielsen, R. B.; Dewan, J. C. Organometallics 1988, 7, 2324-28.
35. Ring-opening reactions of cyclic phosphines are very rare. See: (a) Quin, L. D.; Hughes, A. N. In The Chemistry of Organophosphorus Compounds; Pataï, P., Series Ed.; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1990; Vol. 1, Chapter 10. (b) Quin, L. D.; Roser, C. E. J. Org. Chem. 1974, 23, 3423.
36. Ring-opening reactions of cyclic phosphines are very rare. See: (a) Quin, L. D.; Hughes, A. N. In The Chemistry of Organophosphorus Compounds; Pataï, P., Series Ed.; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1990; Vol. 1, Chapter 10. (b) Quin, L. D.; Roser, C. E. J. Org. Chem. 1974, 23, 3423.
37. 19OPS: C, 66.18; H, 6.59. Found: C, 66.12; H, 6.54.
38. Zablocka, M.; Igau, A.; Majorai, J. P.; Pietrusiewicz, K. M. Organometallics 1993, 12, 603.
39. 21OPS: C, 67.08; H, 6,95. Found: C, 66.85; H, 7.02.
40. Erker, G.; Schlund, R.; Albrecht, M.; Sarter, C. J. Organomet. Chem. 1988, 353, C27.
41. Herberich, G. E.; Boveleth, W.; Hessner, B.; Hostalek, M.; Köffer, D. P. J.; Ohst, H.; Söhnen, D. Chem. Ber. 1986, 119, 420.
42. Wakefield, B. J. In Comprehensive Orgenic Chemistry; Fleming, I., Ed.; Pergamon Press: London, 1991; Vol. 7, pp 85-87.
43. Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
44. Manuel, G.; Mazerolles, P.; Cauquy, G. Syn. React. Inorg. Metal-Org. Chem. 1974, 4, 133.
45. Manuel, G.; Mazerolles, P.; Darbon, J. M. J. Organomet. Chem. 1973, 59, C7.